Moby: 'When you are the only child of a single parent and you have a very complicated relationship with that single parent, their dying is complicated.' Photograph: Adam Taylor/Newspix/REX

I grew up as an only child to a single mother in an incredibly wealthy town in Connecticut but my mother and I were very, very poor. We were on welfare while all of my friends' parents were stockbrokers or heads of corporations. I also grew up in a very culturally conservative town, but my mother and her friends were all pot-smoking hippies.

My father died in a drink-driving accident when I was two and I know this sounds like a Kris Kristofferson lyric, but it's hard to miss something you've never known. Everyone else I knew had two parents and I didn't, but I didn't think it was particularly tragic or strange. Friends of mine lost parents or siblings as they got older; I think that's a lot more tragic and a lot sadder because you've had a life with someone and then they're taken away –but I had no real recollection of my father.

Some of my mother's boyfriends were terrifying. To put it into perspective, all my friends' parents were these very preppy, very neatly groomed Connecticut dads but I remember being taken to Indian Guide, which is a sort of boy scout group for kids, when I was five or six by my mum's boyfriend at the time. He was in a motorcycle gang and he had a huge bushy beard and was basically homeless when he wasn't living with us. He thought it would be funny to show up really, really high so all of these suburban preppy dads were there with my friends and I showed up with this huge Hell's Angel, out of his mind stoned. So there wasn't a lot of paternal comfort there for me. This created the entire subtext to my childhood of me just wishing that I could have a normal childhood, but I only expressed that unease through crippling emotional issues. I never said anything out loud. I bottled everything up. I just assumed that my lot in life was to be a sad, vaguely ashamed outsider.

There were also many positives. All my mother wanted was for me to spend my life being creative. She would have been profoundly disappointed had I become a lawyer or a doctor. From an early age I was just encouraged to make music and take pictures and draw and write. Everyone in the household I grew up in was very culturally progressive and, hopefully not in a pretentious way, also very intellectual. My grandparents, aunts and uncles were all hyper-nerdy intellectual hippies. They'd be smoking pot but they'd also be discussing Derrida and modes of alienation, so that's where I think my early love of philosophy came from, which led me to study it at university. There was a huge focus on education and intelligence but also on the virtues of open-mindedness to almost everything from sexual mores, economics, politics, spirituality and religion and also an assumption that the status quo was probably outdated and not all that helpful.

My grandparents were always a comforting source of stability. My maternal grandmother volunteered at our Presbyterian church and my grandfather had been in the military and been a football player, and he also ran a successful company on Wall Street, so there was a lot of very conventional stability there. Then my father's mother; I would see her about once a year and she was a wonderful woman. I just didn't know her that well.

My mother died in 1998, a year before my album Play was released and the truth is, when you are the only child of a single parent and you have a very complicated relationship with that single parent, their dying is complicated. From an early age she and I were really good friends. When she died it actually felt less like losing a parent and more like losing a really close confidante and friend.

One of the most complicated things about grief is dealing with the regrets of the person who has died. Of course you miss the person but you look at their life and you deal with the disappointments that they've had; their frustrations. When someone dies you ask yourself, "What can I learn from both their successes and their failures? What did they do that I want to emulate and what didn't they do that I'd like to learn from?"

My mother dealt with a lot of insecurities and was inhibited by fear, and I try to be aware of the role of fear in my life and how much of an inhibitory influence it's having on me.

I'd love to have children and it is one of my regrets that I don't, but I'm 48 and single so I don't know when that might actually happen. I see a lot of my aunts and uncles and the way my family has evolved is really fascinating because my aunts and my cousins have all married very far from our white, Anglo-Saxon, Protestant background. Most of them have married people from South America so now when I go home to my aunt and uncles' houses I mainly hear people speaking Spanish.

I feel really fortunate because I'm close to the family that I have – close by choice. A lot of people I know are close to their families but deep down don't really like them that much. Luckily, most of my family are really smart, creative and funny so when we meet up it's a happy choice and not a grim obligation.